FI109791B - Menetelmä taksaanijohdannaisten valmistamiseksi, menetelmän lähtöaine ja välituote - Google Patents

Menetelmä taksaanijohdannaisten valmistamiseksi, menetelmän lähtöaine ja välituote Download PDF

Info

Publication number: FI109791B
Authority: FI; Finland
Prior art keywords: radicals; carbon atoms; radical; general formula; acid
Prior art date: 1992-10-05

Application number

FI951591A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI951591L (fi

FI951591A0 (fi

Inventor

Eric Didier

Alain Commergon

Elie Fouque

Original Assignee

Aventis Pharma Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-10-05

Filing date

1995-04-04

Publication date

2002-10-15

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9434120&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=FI109791(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1995-04-04 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

1995-04-04 Publication of FI951591L publication Critical patent/FI951591L/fi

1995-04-04 Publication of FI951591A0 publication Critical patent/FI951591A0/fi

2002-10-15 Application granted granted Critical

2002-10-15 Publication of FI109791B publication Critical patent/FI109791B/fi

Links

DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 title claims abstract description 4
238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 4
239000007858 starting material Substances 0.000 title 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
239000002253 acid Substances 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 claims abstract description 9
230000032050 esterification Effects 0.000 claims abstract description 7
238000005886 esterification reaction Methods 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
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-1 alkyl radical Chemical class 0.000 claims description 93
125000004432 carbon atom Chemical group C* 0.000 claims description 52
150000001875 compounds Chemical class 0.000 claims description 30
125000006239 protecting group Chemical group 0.000 claims description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
150000003254 radicals Chemical class 0.000 claims description 23
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
150000002148 esters Chemical class 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical group C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 8
150000008064 anhydrides Chemical class 0.000 claims description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
150000005840 aryl radicals Chemical class 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
150000002170 ethers Chemical class 0.000 claims description 7
150000002825 nitriles Chemical class 0.000 claims description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
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150000002576 ketones Chemical class 0.000 claims description 5
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
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229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
229940098779 methanesulfonic acid Drugs 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
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HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
125000005107 alkyl diaryl silyl group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
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239000011737 fluorine Substances 0.000 claims description 3
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238000006467 substitution reaction Methods 0.000 claims description 3
125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
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PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
240000007124 Brassica oleracea Species 0.000 claims description 2
235000003899 Brassica oleracea var acephala Nutrition 0.000 claims description 2
235000011301 Brassica oleracea var capitata Nutrition 0.000 claims description 2
235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims description 2
229910052684 Cerium Inorganic materials 0.000 claims description 2
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
125000005239 aroylamino group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
150000008065 acid anhydrides Chemical class 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
230000003213 activating effect Effects 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
125000005110 aryl thio group Chemical group 0.000 claims 1
150000004200 baccatin III derivatives Chemical class 0.000 claims 1
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims 1
150000008282 halocarbons Chemical class 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
239000007800 oxidant agent Substances 0.000 claims 1
150000003839 salts Chemical class 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 abstract description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 3
150000001602 bicycloalkyls Chemical group 0.000 abstract description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
238000010511 deprotection reaction Methods 0.000 abstract 1
230000008030 elimination Effects 0.000 abstract 1
238000003379 elimination reaction Methods 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
125000003107 substituted aryl group Chemical group 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 79
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 41
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
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238000010168 coupling process Methods 0.000 description 16
238000005859 coupling reaction Methods 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
239000000126 substance Substances 0.000 description 15
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
238000002329 infrared spectrum Methods 0.000 description 14
238000001914 filtration Methods 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
238000004821 distillation Methods 0.000 description 9
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 8
125000004356 hydroxy functional group Chemical group O* 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
238000010908 decantation Methods 0.000 description 5
238000001035 drying Methods 0.000 description 5
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 5
229940011051 isopropyl acetate Drugs 0.000 description 5
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 5
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
PLRPKVNZGONHKD-UHFFFAOYSA-N 1,3-oxazolidine-5-carboxylic acid Chemical compound OC(=O)C1CNCO1 PLRPKVNZGONHKD-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
229940123237 Taxane Drugs 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
238000003556 assay Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
HOJZAHQWDXAPDJ-UHFFFAOYSA-N 3-anilino-2-hydroxypropanoic acid Chemical compound OC(=O)C(O)CNC1=CC=CC=C1 HOJZAHQWDXAPDJ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
150000003927 aminopyridines Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 3
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
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BHTRKISIDQZUQX-NWDGAFQWSA-N (2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H]([C@@H](O)C(O)=O)CC1=CC=CC=C1 BHTRKISIDQZUQX-NWDGAFQWSA-N 0.000 description 2
NNHYAHOTXLASEA-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methoxybenzene Chemical compound COC(OC)C1=CC=C(OC)C=C1 NNHYAHOTXLASEA-UHFFFAOYSA-N 0.000 description 2
LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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229930012538 Paclitaxel Natural products 0.000 description 2
239000012190 activator Substances 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
239000002585 base Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
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150000007529 inorganic bases Chemical class 0.000 description 2
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
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229960001592 paclitaxel Drugs 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
DATOWRNIUXJMDN-LSDHHAIUSA-N (2R,3S)-3-benzamido-2-hydroxy-4-phenylbutanoic acid Chemical compound C([C@@H]([C@@H](O)C(O)=O)NC(=O)C=1C=CC=CC=1)C1=CC=CC=C1 DATOWRNIUXJMDN-LSDHHAIUSA-N 0.000 description 1
KLBMMNQENRBVRI-RCCFBDPRSA-N (2r,4s,5r)-3-[(2-methylpropan-2-yl)oxycarbonyl]-2,4-diphenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound C1([C@H]2[C@@H](O[C@@H](N2C(=O)OC(C)(C)C)C=2C=CC=CC=2)C(O)=O)=CC=CC=C1 KLBMMNQENRBVRI-RCCFBDPRSA-N 0.000 description 1
RDVJYGYJBUIIOE-QZNHQXDQSA-N (2r,4s,5r)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound C1=CC(OC)=CC=C1[C@@H]1N(C(=O)C=2C=CC=CC=2)[C@@H](C=2C=CC=CC=2)[C@H](C(O)=O)O1 RDVJYGYJBUIIOE-QZNHQXDQSA-N 0.000 description 1
HKLKZKAUYDPRFA-ABZYKWASSA-N (4s,5r)-2-(2,4-dimethylphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound CC1=CC(C)=CC=C1C1N(C(=O)OC(C)(C)C)[C@@H](C=2C=CC=CC=2)[C@H](C(O)=O)O1 HKLKZKAUYDPRFA-ABZYKWASSA-N 0.000 description 1
HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
MYIPEPGIRJMNHF-UHFFFAOYSA-N 2,3,4-trimethyl-3-(2,3,4-trimethylpentan-3-yloxy)pentane Chemical compound CC(C)C(C)(C(C)C)OC(C)(C(C)C)C(C)C MYIPEPGIRJMNHF-UHFFFAOYSA-N 0.000 description 1
YKELHZJMSIWDHU-FTLRAWMYSA-N 3-o-tert-butyl 5-o-methyl (4s,5r)-2-methoxy-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate Chemical compound CC(C)(C)OC(=O)N1C(OC)O[C@@H](C(=O)OC)[C@@H]1C1=CC=CC=C1 YKELHZJMSIWDHU-FTLRAWMYSA-N 0.000 description 1
WTQDGOCRQVFUFA-UHFFFAOYSA-N 4-(Dimethoxymethyl)-1,2-dimethoxybenzene Chemical compound COC(OC)C1=CC=C(OC)C(OC)=C1 WTQDGOCRQVFUFA-UHFFFAOYSA-N 0.000 description 1
OJHMZGCNWLTEMV-UHFFFAOYSA-N 4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound OC(=O)C1OCNC1C1=CC=CC=C1 OJHMZGCNWLTEMV-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
235000001674 Agaricus brunnescens Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000006011 chloroethoxy group Chemical group 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
ATVZDBNSVOOCMZ-UHFFFAOYSA-N methyl 2-phenyl-1,3-oxazolidine-5-carboxylate Chemical compound O1C(C(=O)OC)CNC1C1=CC=CC=C1 ATVZDBNSVOOCMZ-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000002917 oxazolidines Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
125000005000 thioaryl group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

FI951591A 1992-10-05 1995-04-04 Menetelmä taksaanijohdannaisten valmistamiseksi, menetelmän lähtöaine ja välituote FI109791B (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR9211742A FR2696459B1 (fr)	1992-10-05	1992-10-05	Procédé de préparation de dérivés du taxane.
FR9211742		1992-10-05
FR9300968		1993-10-04
PCT/FR1993/000968 WO1994007878A1 (fr)	1992-10-05	1993-10-04	Procede de preparation de derives du taxane

Publications (3)

Publication Number	Publication Date
FI951591L FI951591L (fi)	1995-04-04
FI951591A0 FI951591A0 (fi)	1995-04-04
FI109791B true FI109791B (fi)	2002-10-15

Family

ID=9434120

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI951591A FI109791B (fi)	1992-10-05	1995-04-04	Menetelmä taksaanijohdannaisten valmistamiseksi, menetelmän lähtöaine ja välituote

Country Status (31)

Country	Link
US (1)	US5637723A (zh)
EP (1)	EP0663907B1 (zh)
JP (1)	JP3014761B2 (zh)
KR (1)	KR100297197B1 (zh)
CN (1)	CN1048983C (zh)
AT (1)	ATE147735T1 (zh)
AU (1)	AU689081B2 (zh)
CA (1)	CA2146155C (zh)
CZ (1)	CZ283362B6 (zh)
DE (1)	DE69307527T2 (zh)
DK (1)	DK0663907T3 (zh)
EE (1)	EE03125B1 (zh)
ES (1)	ES2096329T3 (zh)
FI (1)	FI109791B (zh)
FR (1)	FR2696459B1 (zh)
GE (1)	GEP19981299B (zh)
GR (1)	GR3022285T3 (zh)
HU (1)	HU223775B1 (zh)
LT (1)	LT3439B (zh)
LV (1)	LV10858B (zh)
MX (1)	MX9305767A (zh)
NO (1)	NO310412B1 (zh)
NZ (1)	NZ256446A (zh)
PL (1)	PL179147B1 (zh)
RU (1)	RU2116302C1 (zh)
SG (1)	SG63619A1 (zh)
SK (1)	SK280624B6 (zh)
TW (1)	TW262471B (zh)
UA (1)	UA43835C2 (zh)
WO (1)	WO1994007878A1 (zh)
ZA (1)	ZA937319B (zh)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6794523B2 (en)	1991-09-23	2004-09-21	Florida State University	Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them
FR2697522B1 (fr) *	1992-10-30	1994-11-25	Rhone Poulenc Rorer Sa	Procédé de préparation de dérivés du taxane.
FR2698361B1 (fr) *	1992-11-20	1995-01-13	Rhone Poulenc Rorer Sa	Procédé de préparation d'un acide oxazolidine-1,3 carboxylique-5.
FR2698871B1 (fr)	1992-12-09	1995-02-24	Rhone Poulenc Rorer Sa	Nouveau taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.
IL107950A (en)	1992-12-15	2001-04-30	Upjohn Co	b 7, b 8 - Matano - Taxols, their preparation and pharmaceutical preparations against malignant tumors containing them
ES2145829T3 (es) *	1993-06-11	2000-07-16	Upjohn Co	Uso antineoplasico de delta 6,7-taxoles y composiciones farmaceuticas que los contienen.
FR2706457B1 (fr) *	1993-06-16	1995-07-28	Rhone Poulenc Rorer Sa	Procédé de préparation d'un acide oxazolidinecarboxylique utile pour préparer des taxoïdes thérapeutiquement actifs.
IL112412A (en) *	1994-01-28	2000-02-29	Upjohn Co	Delta 12,13-iso-taxol analogs and antineoplastic pharmaceutical compositions containing them
CA2170661A1 (en) *	1995-03-22	1996-09-23	John K. Thottathil	Novel methods for the preparation of taxanes using oaxzolidine intermediates
US5847170A (en) *	1995-03-27	1998-12-08	Rhone-Poulenc Rorer, S.A.	Taxoids, their preparation and pharmaceutical compositions containing them
US6372780B2 (en)	1995-03-27	2002-04-16	Aventis Pharma S.A.	Methods of treating cell lines expressing multidrug resistance P-glycoprotein
MA23823A1 (fr)	1995-03-27	1996-10-01	Aventis Pharma Sa	Nouveaux taxoides, leur preparation et les compositions qui les contiennent
EP0868422A1 (de) *	1996-09-24	1998-10-07	Marigen S.A.	Ultramikroemulsionen aus spontan dispergierbaren konzentraten mit antitumoral und antiviral wirksamen estern von baccatin-iii-verbindungen
FR2771092B1 (fr) *	1997-11-18	1999-12-17	Rhone Poulenc Rorer Sa	Procede de preparation de derives de la classe des taxoides
US6096250A (en) *	1998-03-06	2000-08-01	Caesar International, Inc.	Process for releasing a runner from an electronic device package on a laminate plate
US6156789A (en) *	1998-03-17	2000-12-05	Rhone-Poulenc Rorer S.A.	Method for treating abnormal cell proliferation in the brain
US6346543B1 (en)	1998-08-17	2002-02-12	Aventis Pharma S.A.	Use of a taxoid to treat abnormal cell proliferation in the brain
US6403634B1 (en)	1999-01-13	2002-06-11	Aventis Pharma S.A.	Use of taxoid derivatives
IT1308636B1 (it)	1999-03-02	2002-01-09	Indena Spa	Procedimento per la preparazione di tassani da 10-desacetilbaccatinaiii.
AU775373B2 (en)	1999-10-01	2004-07-29	Immunogen, Inc.	Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
WO2002066448A1 (en) *	2001-02-20	2002-08-29	Dabur India Limited	Method of preparation of paclitaxel (taxol) using 3-(alk-2-ynyloxy) carbonyl-5-oxazolidine carboxylic acid
DE01924282T1 (de) *	2001-03-23	2007-04-19	Scinopharm Taiwan, Ltd.	Verfahren zur herstellung von taxanderivaten
US6891050B2 (en) *	2001-08-10	2005-05-10	Dabur India Limited	Process for the preparation of taxanes such as paclitaxel, docetaxel and structurally similar analogs
US6881852B2 (en) *	2002-02-05	2005-04-19	Dabur India Limited	Process of purification of paclitaxel and docetaxel
US7247738B2 (en) *	2002-05-07	2007-07-24	Dabur India Limited	Method of preparation of anticancer taxanes using 3-[(substituted-2-trialkylsilyl) ethoxycarbonyl]-5-oxazolidine carboxylic acids
US6900342B2 (en) *	2002-05-10	2005-05-31	Dabur India Limited	Anticancer taxanes such as paclitaxel, docetaxel and their structural analogs, and a method for the preparation thereof
US6838569B2 (en)	2002-12-16	2005-01-04	Dabur India Limited	Process for preparation of paclitaxel trihydrate and docetaxel trihydrate
FR2882362B1 (fr) *	2005-02-23	2007-05-11	Seripharm	Procede de preparation du paclitaxel
AU2007309534B2 (en) *	2006-10-20	2012-08-16	Scinopharm Singapore Pte, Ltd.	Process for making crystalline anhydrous docetaxel
PL210984B1 (pl) *	2006-10-31	2012-03-30	Inst Farmaceutyczny	Sposób wytwarzania docetakselu
KR100847331B1 (ko) *	2006-12-14	2008-07-21	한미약품 주식회사	도세탁셀의 제조방법 및 이에 사용되는 중간체
KR100921036B1 (ko)	2006-12-18	2009-10-08	한미약품 주식회사	탁산유도체의 제조방법 및 이에 사용되는 중간체
KR101671537B1 (ko)	2008-08-11	2016-11-01	넥타르 테라퓨틱스	다분지형 중합체 알카노에이트 컨쥬게이트
PL388144A1 (pl)	2009-05-29	2010-12-06	Przedsiębiorstwo Produkcyjno-Wdrożeniowe Ifotam Spółka Z Ograniczoną Odpowiedzialnością	Solwaty (2R,3S)-3-tert-butoksykarbonylamino-2-hydroksy-3-fenylopropionianu 4-acetoksy-2α-benzoiloksy -5β,20-epoksy-1,7β,10β-trihydroksy-9-okso-taks-11-en-13α-ylu, sposób ich otrzymywania i zastosowanie
WO2011134067A1 (en) *	2010-04-29	2011-11-03	6570763 Canada Inc.	Novel amino acid molecule and uses thereof
US20130331443A1 (en)	2010-12-22	2013-12-12	Nektar Therapeutics	Multi-arm polymeric prodrug conjugates of taxane-based compounds
US10894087B2 (en)	2010-12-22	2021-01-19	Nektar Therapeutics	Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds
WO2012088433A1 (en)	2010-12-22	2012-06-28	Nektar Therapeutics	Deuterated and/or fluorinated taxane derivatives
EP2760848B1 (en)	2011-09-26	2018-11-28	Fresenius Kabi Oncology Limited	Processes for the preparation of cabazitaxel involving c(7)-oh and c(13)-oh silylation or just c(7)-oh silylation
KR101379694B1 (ko)	2011-09-30	2014-03-31	주식회사 삼양바이오팜	탁산유도체의 제조방법
CN102382080B (zh) *	2011-12-15	2014-06-18	扬子江药业集团江苏海慈生物药业有限公司	一种多西他赛的制备方法
FR2986526A1 (fr) *	2012-02-03	2013-08-09	Sanofi Sa	Procede de preparation de derives du taxol et certains composes intermediaires
CN104650012A (zh) *	2013-11-22	2015-05-27	天士力控股集团有限公司	一种紫杉烷类化合物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2601675B1 (fr)	1986-07-17	1988-09-23	Rhone Poulenc Sante	Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent
MX9102128A (es) *	1990-11-23	1992-07-08	Rhone Poulenc Rorer Sa	Derivados de taxano,procedimiento para su preparacion y composicion farmaceutica que los contiene
FR2687151B1 (fr) *	1992-02-07	1994-03-25	Rhone Poulenc Rorer Sa	Nouveaux derives de la baccatine iii et de la desacetyl-10 baccatine iii, leur preparation et les compositions pharmaceutiques qui les contiennent.
US5440056A (en) *	1992-04-17	1995-08-08	Abbott Laboratories	9-deoxotaxane compounds

1992
- 1992-10-05 FR FR9211742A patent/FR2696459B1/fr not_active Expired - Fee Related
1993
- 1993-04-10 UA UA95038242A patent/UA43835C2/uk unknown
- 1993-09-21 MX MX9305767A patent/MX9305767A/es unknown
- 1993-09-28 CN CN93118203A patent/CN1048983C/zh not_active Expired - Lifetime
- 1993-10-01 ZA ZA937319A patent/ZA937319B/xx unknown
- 1993-10-02 TW TW082108115A patent/TW262471B/zh not_active IP Right Cessation
- 1993-10-04 JP JP6508788A patent/JP3014761B2/ja not_active Expired - Lifetime
- 1993-10-04 CA CA002146155A patent/CA2146155C/fr not_active Expired - Lifetime
- 1993-10-04 DK DK93921983.8T patent/DK0663907T3/da active
- 1993-10-04 RU RU95110686A patent/RU2116302C1/ru active
- 1993-10-04 WO PCT/FR1993/000968 patent/WO1994007878A1/fr active IP Right Grant
- 1993-10-04 US US08/406,985 patent/US5637723A/en not_active Expired - Lifetime
- 1993-10-04 KR KR1019950701303A patent/KR100297197B1/ko not_active Expired - Lifetime
- 1993-10-04 NZ NZ256446A patent/NZ256446A/en not_active IP Right Cessation
- 1993-10-04 AU AU51151/93A patent/AU689081B2/en not_active Expired
- 1993-10-04 AT AT93921983T patent/ATE147735T1/de active
- 1993-10-04 GE GEAP19932473A patent/GEP19981299B/en unknown
- 1993-10-04 LV LVP-93-1121A patent/LV10858B/lv unknown
- 1993-10-04 SK SK435-95A patent/SK280624B6/sk not_active IP Right Cessation
- 1993-10-04 EP EP93921983A patent/EP0663907B1/fr not_active Expired - Lifetime
- 1993-10-04 DE DE69307527T patent/DE69307527T2/de not_active Expired - Lifetime
- 1993-10-04 PL PL93308306A patent/PL179147B1/pl unknown
- 1993-10-04 HU HU9500967A patent/HU223775B1/hu active IP Right Grant
- 1993-10-04 CZ CZ95842A patent/CZ283362B6/cs not_active IP Right Cessation
- 1993-10-04 LT LTIP1396A patent/LT3439B/lt not_active IP Right Cessation
- 1993-10-04 ES ES93921983T patent/ES2096329T3/es not_active Expired - Lifetime
- 1993-10-04 SG SG1996007545A patent/SG63619A1/en unknown
1994
- 1994-11-18 EE EE9400361A patent/EE03125B1/xx unknown
1995
- 1995-03-29 NO NO19951202A patent/NO310412B1/no not_active IP Right Cessation
- 1995-04-04 FI FI951591A patent/FI109791B/fi not_active IP Right Cessation
1997
- 1997-01-16 GR GR960402651T patent/GR3022285T3/el unknown

Also Published As

Publication number	Publication date
CA2146155C (fr)	2003-03-11
PL179147B1 (pl)	2000-07-31
JP3014761B2 (ja)	2000-02-28
SG63619A1 (en)	1999-03-30
NZ256446A (en)	1996-06-25
KR950703547A (ko)	1995-09-20
FI951591L (fi)	1995-04-04
ATE147735T1 (de)	1997-02-15
FI951591A0 (fi)	1995-04-04
LT3439B (en)	1995-10-25
EP0663907B1 (fr)	1997-01-15
NO951202D0 (no)	1995-03-29
RU2116302C1 (ru)	1998-07-27
HU9500967D0 (en)	1995-06-28
US5637723A (en)	1997-06-10
HUT72612A (en)	1996-05-28
MX9305767A (es)	1994-05-31
TW262471B (zh)	1995-11-11
EP0663907A1 (fr)	1995-07-26
SK280624B6 (sk)	2000-05-16
PL308306A1 (en)	1995-07-24
HU223775B1 (hu)	2005-01-28
FR2696459A1 (fr)	1994-04-08
LV10858B (en)	1996-06-20
WO1994007878A1 (fr)	1994-04-14
DE69307527D1 (de)	1997-02-27
CN1048983C (zh)	2000-02-02
JPH08501789A (ja)	1996-02-27
NO951202L (no)	1995-03-29
CN1087905A (zh)	1994-06-15
AU5115193A (en)	1994-04-26
AU689081B2 (en)	1998-03-26
LV10858A (lv)	1995-10-20
ES2096329T3 (es)	1997-03-01
UA43835C2 (uk)	2002-01-15
RU95110686A (ru)	1996-12-27
CZ283362B6 (cs)	1998-03-18
DE69307527T2 (de)	1997-05-22
SK43595A3 (en)	1995-08-09
DK0663907T3 (da)	1997-02-03
KR100297197B1 (ko)	2001-11-26
LTIP1396A (en)	1995-01-31
ZA937319B (en)	1994-04-22
GR3022285T3 (en)	1997-04-30
CA2146155A1 (fr)	1994-04-14
EE03125B1 (et)	1998-10-15
CZ84295A3 (en)	1995-09-13
NO310412B1 (no)	2001-07-02
GEP19981299B (en)	1998-05-01
FR2696459B1 (fr)	1994-11-25

Publication	Publication Date	Title
FI109791B (fi)	2002-10-15	Menetelmä taksaanijohdannaisten valmistamiseksi, menetelmän lähtöaine ja välituote
US5677462A (en)	1997-10-14	Process for preparing taxane derivatives
US5726318A (en)	1998-03-10	Process for the preparation of taxane derivatives
US5977375A (en)	1999-11-02	Esters of baccatin III and 10-deacetylbaccatin III
FI109798B (fi)	2002-10-15	Menetelmä taksaanivälituotteiden valmistamiseksi, lähtöaineet taksaanivälituotteiden valmistamiseksi ja taksaanivälituotteet
FI119289B (fi)	2008-09-30	Menetelmä (4S, 5R)-1,3-oksatsolidin-5-karboksyylihapon valmistamiseksi ja menetelmä taksaanijohdannaisten valmistamiseksi näin saatua karboksyylihappoa käyttäen

Legal Events

Date	Code	Title	Description
2013-11-29	MA	Patent expired